4-Nitroperhydropyrido[1,2-a][1,4]diazepines

Abstract

Compounds of the formula v,2/12 Wherein R 1 is H, lower-alkyl, hydroxyalkyl, phenyl, aralkyl, or --(CH 2 ) n --X wherein n is 0-4 and X is --COO-lower-alkyl, C.tbd.N or --COOH and R 2 is H, lower-alkyl or aralkyl, produced by condensing a diamine of the formula ##SPC1## With a nitro compound of the formula R 1 --CH 2 --NO 2 in the presence of formalin or paraformaldehyde, or with the R 1 -- C(CH 2 OH) 2 NO 2 reaction product of the above nitro compound and formalin or paraformaldehyde, or with formalin or paraformaldehyde followed by reaction with the above nitro compound, and their acid addition salts, possess antimicrobial activity against both gram-positive and gram-negative bacteria and also against dermatophytes, yeasts and other fungi.

1. A compound of the formula ##SPC5## wherein R 1  is a hydrogen atom, alkyl of 1--12 carbon atoms, phenyl, hydrocarbon monocycle aralkyl of 7-10 carbon atoms, hydroxyalkyl of 1-4 carbon atoms, or --(CH 2 ) n  --X wherein n is an integer from 0-4, inclusive and X is alkoxycarbonyl of 1-4 carbon atoms in the alkoxy group, nitrile, or carboxy, and R 2  is a hydrogen atom, alkyl of 1--4 carbon atoms or hydrocarbon monocyclic aralkyl of 7--10 carbon atoms, or a   
     
     
       5. A compound of claim 1 wherein R 1  is --(CH 2 ) n  --C.tbd.N 
     
     
       6. A compound of claim 1 wherein R 1  is --(CH 2 ) n  --CO-alkoxy wherein n has the values given therein and alkoxy is of 1-4 carbon atoms. 
     
     
       7. A compound of claim 1 wherein R 1  is --(CH 2 ) n  OH wherein n 
     
     
       9. 2,4-Dimethyl-4-nitroperhydropyrido[1,2-a][1,4]diazepine, a compound of 
     
     
       10. 2,4-Dimethyl-4-nitroperhydropyrido[1,2-a][1,4]diazepine 
     
     
       11. 4-Ethyl-2-methyl-4-nitroperhydropyrido[1,2-a][1,4]diazepine 
     
     
       12. 4-n-Butyl-2-methyl-4-nitroperhydropyrido[1,2-a][1,4]diazepine 
     
     
       13. 4-(2-Methoxycarbonylethyl)-2-methyl- 
     
     
       14. 4-(2-Methoxycarbonylethyl)-2-methyl-4-nitroperhydropyrido[1,2- 
     
     
       15. 4-(2-Cyanoethyl)-2-methyl-4-nitroperhydropyrido[1,2-a]-[1,4]diazepine 
     
     
       16. 2-Methyl-4-nitro-4-n-propylperhydropyrido[1,2-a][1,4]-diazepine 
     
     
       17. 4-Isobutyl-2-methyl-4-nitroperhydropyrido [1,2-a][1,4]-diazepine 
     
     
       18. 2-Methyl-4-nitro-4-n-pentylperhydropyrido[1,2-a][1,4]-diazepine 
     
     
       19. 2-Methyl-4-nitro-4-undecylperhydropyrido[1,2-a][1,4]-diazepine 
     
     
       20. 2-Methyl-4-nitro-4-phenylperhydropyrido[1,2-a][1,4]-diazepine 
     
     
       21. 2-Benzyl-4-n-butyl-4-nitroperhydropyrido[1,2-a][1,4]-diazepine 
     
     
       22. 4-Hydroxymethyl-2-methyl-4-nitroperhydropyrido-[1,2-a][1,4]diazepine 
     
     
       23. 2-Methyl-4-nitroperhydropyrido[1,2-a][1,4]diazepine dihydrochloride, a 
     
     
       24. 4-Methoxycarbonyl-2-methyl-4-nitroperhydropyrido-[1,2-a][1,4]diazepine 
     
     
       25. 4-Benzyl-2-methyl-4-nitroperhydropyrido[1,2-a][1,4]-diazepine 
     
     
       26. 4-Hexyl-2-methyl-4-nitroperhydropyrido[1,2-a][1,4]-diazepine 
     
     
       27. 4-Heptyl-2-methyl-4-nitroperhydropyrido[1,2-a][1,4]-diazepine dihydrochloride, a compound of claim 1.